Tobacco product



United States Patent 3,389,706 TOBACCO PRODUCT Joseph N. Schumacher, Winston-Saiem, N.C., assignor to R. J. Reynolds Tobacco Company, Winston-Salem, N.C., a corporation of New Jersey No Drawing. Filed Nov. 8, 1965, Ser. No. 506,863 3 Claims. (Cl. 13117) This invention relates to a tobacco product and has for an object the provision of a composition and process for improving the flavor and aroma of tobacco and tobacco smoke.

It is well known in the tobacco art that the flavor and aroma of the tabacco product and the smoke from the tobacco are very important considerations in so far as the ultimate consumer is concerned. Considerable efforts are exertedby the manufacturers of tobacco products to provide a product that will be acceptable to the consumer, particularly as regards flavor and aroma characteristics. It has been the common practice in the tobacco industry to prepare blends of domestic and oriental tobaccos in order to provide smoking tobacco which has a pleasing flavor and aroma before and during smoking. However, such a procedure is costly and may at times become prohibitive in the event that certain types of tobacco may be in short supply. Accordingly, it is a further object of this invention to provide a new class of additive materials which when applied to the tobacco products improve and enhance the flavor and aroma of these products and the smoke emitted therefrom thereby increasing or enhancing the pleasure and other values that may be derived by the consumer from the use of these products.

A further object of this invention is the provision of a process for enhancing or otherwise improving the flavor, aroma and other qualities of certain domestic, oriental, reconstituted or synthetic tobaccos which may be deficient in said flavor or aroma or other qualities.

An additional object of this invention is to provide a process of preparing a smoking tobacco or product which when smoked has an enhanced flavor or aroma.

A still further object of this invention is the provision of smoking products, such as cigarettes, cigars or pipe tobacco, and a process for forming same whereby the flavor and aroma before and during smoking are improved or enhanced.

Further and additional objects will appear from the following description and the appended claims.

In accordance with one embodiment of this invention, a tobacco product is provided to which has been added or which has been treated with a small amount of 2,3,6,7,- 8,8a hexahydro 7 oxo 2,5,5,8a tetramethyl 5H 1- benzopyran (hereinafter called Compound I). Compound I can be illustrated by the formula:

A. SYNTHESIS AND PROPERTIES OF 2,3,6,7,8,8a- HEXAHYDRO 7 OX0 2,5,5,8a TETRAMETH- LY-SH-l-BENZOPYRAN (1) 5-OXO-zx-i0n0nfi or also known as 4-(4-oxo-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one The method of V. Prelog and M. Osgan, Helv. Chim. Acta, 35, 986-92 (1952), or modifications of it, was used for the preparation of 5OXO-OL-lOnOl'l6. a-Ionone grams) was treated with t-butyl chromate in carbon tetrachloride (325 grams t-butyl alcohol, 220 grams chromic anhydride, 200 milliliters acetic acid, 30 milliliters acetic anhydride, and 2 liters carbon tetrachloride). The mixture was kept at 0 C. for 16 days in the dark, after which time it was worked up in the prescribed manner. The material obtained was chromatographed, and 40 grams of a-ionone, 1.5 grams of 4-oxo-fi-ionone or also known as 4 (3 oxo 2,6,6 trimethyl 1 cyclohexen 1 yl)- 3 buten- 2 one, and 12 grams of 5-oxo-a-ionone were obtained as pure compounds. The 5-oxo-a-ionone was recrystallized from pentane-ether solutions and melted at 7173 C. (lit. M.P. 6667).

(2) Rearrangement and cyclization of 5 oxo a ionone.Crude 5-oxo-a-ionone (25 grams) was dissolved in 100 milliliters of 1:1 methyl alcohol/water containing 8 grams of potassium hydroxide and allowed to stand overnight at room temperature. The solution was neutralized, diluted with water, extracted with ether, and the ether was removed in vacuo. The crude dione (II) was dissolved in 25 milliliters of ethanol and two grams of sodium borohydride were added. After standing two hours, the mixture was acidified, diluted with water, and extracted with ether. Removal of the ether in vacuo gave crude keto-alcohol (III).

The keto-alcohol (III) was dissolved in 25 milliliters of benzene containing 0.2 gram of p-toluenesulphonic acid, and the resulting solution was refluxd one hour. The cooled solution was washed with water and with 5 percent sodium carbonate solution. After removing the benzene in vacuo, the residue was distilled, yielding 1.2 grams of 2,3,6,7,8,8a-hexahydro-7-oxo-2,5,5,8a-tetramethyl-5H- l-benzopyran, boiling point 87-89/ 2 millimeters; nuclear magnetic resonance spectrum: u=8.87(3); 817(3); doulet 8.76(3); 851(3); 7.64(2); 7.42(2); 6.15(1); and 427(1).

It has been found that the tobacco additive of the invention when incorporated into tobacco products imparts an ionone flavor and aroma during smoking which many smokers consider to be desirable in smoking products. However, it is pointed out that the methods for defining or characterizing the quality of a flavor or aroma in the tobacco art are almost purely subjective and different smokers may define the same flavor quite differently.

In accordance with this invention, the above indicated compound is added to tobacco or applied to a smoking article or its component parts in amounts of about 0.0001 to 1.0 percent by weight of the product. Preferably the amount of additive is between about 0.01 and 0.5 percent by weight in order to provide a tobacco product having a desired flavor and aroma. However, the amount used will depend upon the amount of flavor and aroma desired and the particular compound or mixture thereof that is used. The additive may be incorporated at any step in the treatment of the tobacco but is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes. Likewise, it will be apparent that only a portion of the tobacco need be treated and the thus treated tobacco may be blended with other tobaccos before the cigarettes or other smoking articles are formed. In such case the tobacco treated may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.

In accordance with one specific embodiment of this invention, an aged flue-cured and shredded tobacco is sprayed with a 1% ethyl alcohol solution of 2,3,6,7,8,8ahexahydro-7-oxo-2,5,5,8a-tetramethyl-5H-1 benzopyran in an amount to provide a tobacco containing 0.1 percent by weight of the additive on a dry basis. Thereafter the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. It has been found that the cigarette when prepared as indicated has a desired and pleasing flavor.

The additive falling within the scope of this invention may be applied to the tobacco by spraying, dipping or otherwise, utilizing suitable suspensions or solutions of the additive. Thus water or volatile organic solvents, such as alcohol, ether, acetone, volatile hydrocarbons and the like, may be used as the carrying medium for the additive while it is being applied to the tobacco. Also, other fiavor and aroma-producing additives, such as those disclosed in U.S. Patents Nos. 2,766,145, 2,905,575, 2,905,- 576, 2,978,365 and 3,034,211 may be incorporated into the tobacco with the additive of this invention.

While this invention is principally useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars or other tobacco products. Furthermore, the compound may be added to certain tobacco substitutes of natural or synthetic origin and by the term tobacco as used throughout this specification is meant any composition intended for human consumption by smoking or otherwise, whether composed of tobacco plant parts or substitute materials or both.

Also, the invention has been particularly described with reference to the addition of the compound directly to tobacco. However, it will be apparent that the compound may be applied to the paper of the cigarette or to the wrapper of a cigar. Also it may be incorporated into the filter tip, the packaging material or the seam paste em ployed for gluing the cigarette paper. Thus, a tobacco product is provided which includes the specified additive and tobacco although in every instance the compound need not be admixed with the tobacco as above specifically described.

While several particular embodiments of this invention are shown above, it will be understood, of course, that the invention is not to be limited thereto, since many modifications may be made, and it is contemplated, therefore, by the appended claims, to cover any such modifications ,as fall within the true spirit and scope of this invention.

I claim:

1. A tobacco product having added thereto 2,3,6,7,8, 8a hexahydro 7 OX0 2,5,5,8a tetramethyl 5H 1- benzopyran in an amount sufiicient to alter the flavor or aroma of the tobacco product.

2. The product recited in claim 1 where in the amount of the compound added to the product is between about 0.0001 and 1.0 percent by weight of the product.

3. The product recited in claim 1 wherein the amount of the compound added to the tobacco product is betweeen about 0.01 and 0.5 percent by weight of the product.

References Cited UNITED STATES PATENTS 3,185,708 5/1965 Mims. 3,217,716 11/1965 Roberts 13117 SAMUEL KOREN, Primary Examiner.

D. J. DONOHUE, Assistant Examiner. 

1. A TOBACCO PRODUCT HAVING ADDED THERETO 2,3,6,7,8, 8A - HEXAHYDRO - 7 - OXO - 2,5,5,8A - TETRAMETHYL - 5H - 1BENZOPYRAN IN AN AMOUNT SUFFICIENT TO ALTER THE FLAVOR OR AROMA OF THE TOBACCO PRODUCT. 